Capannino in Castellina (Chiant) sits on sloping hills with a southwest exposure, looking out…read moreacross classic Chianti countryside. The landscape features vineyard rows follow the natural terrain, and the horizon stretches into nearby historic towns like Monteriggioni, reinforcing how deeply agriculture and history overlap. The vineyard is rooted in tradition, centered on 100% Sangiovese. The soils clay, limestone, and do the heavy lifting, producing wines known for structure, and a clear sense of place: cherry, spice, earth, and that unmistakable Chianti backbone rather than overt richness or flash. It sits within long-standing estate traditions tied to Bibbiano, where viticulture has been passed through generations. And that carries into the experience itself. This is not a polished wine-tour destination with curated tastings and choreographed hospitality. It's quieter, more minimal, and focused almost entirely on the vineyard and what it produces. That simplicity may feel sparse to some, but it's also the point.

Had the privilege of staying in their apartment which was attached to their house. Had wine…read moretastings and olive oil tastings. They have different types of Chianti for you to try. Loved all of them and the olive oil is the best!! They are incredibly warm and friendly. We got to see them use what is left after pressing the grapes for wine and use it for grappa. They work so hard! It's a magical place and if you can stop here, I highly recommend it, the views are amazing!

The tower is the tallest in San Gimignano below is the church and museum. The 13 Euro combo ticket…read moreincludes the Torre Grossa, 4 other museum and church. To visit the tower need physical strength to climb up to the top of tower. There no elevator to take you. But they do have the screen display entire way to the top of the tower. It has different movies and spectacular mechanical display. The view on the top is beautiful. You can see the entire city within the wall. I believe this is a watch tower at the past. It is part of the defense scheme to spot the enemy far away. The tower visit is minimum 1 hour but if you are fast, it can be done in 30 minutes. A bell is at the top of the tower in the steel cage. It can use for the warning of the town, fire, or church bell.

Such an amazing memory of San Gimignano and the panoramic views of the Tuscan Countryside from the…read moreTorre Grossa. A day I will never forget. Thank you for helping me to fall even more in love with Italy.

It's the main gateway into the medieval village of San Gimignano, and not to be confused with the…read morefamous one of the same name in Rome. It's located in front of the Martyrs of Montemaggio Square where there's a war memorial to the fallen of San Gimignano. There's also a beautiful view of the Tuscan countryside as you walk up to this impressive looking gateway. There are many views like that one as you walk along the walls of this ancient town. However, you'll need to overlook the touristy parts of it so that you can truly appreciate and enjoy it.

This town is a MUST stop if going wine tasting through the Tuscan region. Beautiful views of the…read moreTuscan valley from the top with a fantastic shops and restaurants. We got to experience someone reading some beautiful Italian poetry on the top of the hill who we found out is typically doing this daily.

This was actually my favorite piazza in San Gimignano. It's the one with the old cistern, or well…read more There's always a bunch of people sitting on it as they do on the steps in other public squares. What's unusual is that this square is really in the shape of a triangle. You'll also see the Devil's Tower near the cistern. It has been said that the owner returned to find his tower taller than it was when he left it. Lol! That's kind of spooky. What I loved most about this medieval piazza is the famous gelato shop. It was a historical and tasty experience.

This is a lovely piazza/town square in the heart of Sam Gimignano. Admittedly, San Gimignano was…read moreone of my two favorite places visited during my two weeks in Tuscany and this square was absolutely lovely. There is an old cistern (hence its name) in the square along with lots of lovely shops, including a pair of dueling gelato shops (one of which is often featured on travel shows). There are plenty of opportunities for getting your perfect Instagrammable moments here as well.

This is another ancient gate in San Gimignano that served as its second southern gate. The gate,…read morealong with the tower next to it, belonged to the Becci family. A wealthy and prominent merchant that lived there. I still find it fascinating how the architecture and layout of this arch and city is still very well-preserved. It's an UNESCO World Heritage site for a good reason.